How do you decide what to listen to? Same old stuff?

In what areas do you make choices easily and efficiently?  Pay attention to the strategies you are using successfully, and apply them to the “challenging” subjects.  For example, when you choose which shoes or pants to wear, how do you do it, what is the process you go through, to get to the end result?  By limiting your pool of options (movies, wine, music) to two, three, or four choices, making a selection may feel less overwhelming.  Make sense?

I have 'Release Radar' and 'Discover Weekly' on my Spotify. I also listen to Spotify Radio stations of artists that I like then they add artists/songs that are in the same genre---some I've never heard before. I've discovered a lot of new music and new mixes etc of old music. 

I’ve just completed installing IKEA Kallax shelves for vinyl and CDs in our home office, enough to hold about 1,000 LPs and CDs.  I’ve decided to create a system that will allow me to make selections based on genre/mood: for instance, Jazz/Mellow/Upbeat/Experimental  A-Z.  Rock, Folk, Blues, and Classical will be also get subsections pertinent to my moods for each of them too (as much as space allows).  Because, like the OP, I can't  always readily determine what fits the moment or mood.  If my physical collection gets too familiar I can more easily supplement from streaming (Tidal for me), and/or make new purchases based on artists subsections by browsing record stores and magazines like Absolute Sound and others.  I love collecting physical media, LPs, CDs, Books, and Film. its challenging finding space for it all, but its my personal heaven away from the mundane, and my home is the envy of all our like-minded friends when we get together to cozy up to talk books, watch films/shows, and especially listen to great music on the main system. 

If you want surefire like, stick with what you know you like. 

If you feel adventurous, try new material, with the understanding that you will NOT like most of it, but you may make a cool new find. True for wine as for music.

I don't stream, but rather use bandcamp recommendations by artists whom I like, and also from YouTube discussions. Again >95% is not to my liking.

If I can’t decide I use Roon random play.  Or  Roon radio.  I do this a lot.